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- W4327733599 abstract "Abstract We report a synthetic endeavor towards the highly strained pentacyclic caged framework of the mavacuran alkaloids which culminated with the concise total synthesis of C ‐fluorocurine, C ‐profluorocurine, C ‐mavacurine, normavacurine, 16‐ epi ‐pleiocarpamine and taberdivarine H. We designed a strategy involving late‐stage construction of the D ring by Michael addition of a vinylic nucleophile to a 2‐indolyl acrylate moiety. While the intramolecular Michael addition did not succeed, we were able to perform a diastereoselective unusual intermolecular 1,4‐addition of a functionalized vinyl lithium reagent to a readily accessible Michael acceptor with the assistance of the piperidine nitrogen atom through the formation of a complex as suggested by DFT computations. Final cyclization was achieved by nucleophilic substitution to form an ammonium intermediate. The first total syntheses of C ‐profluorocurine and C ‐fluorocurine were finalized by the dihydroxylation of C ‐mavacurine and a pinacol rearrangement, respectively." @default.
- W4327733599 created "2023-03-18" @default.
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- W4327733599 date "2023-04-13" @default.
- W4327733599 modified "2023-10-05" @default.
- W4327733599 title "Collective Total Synthesis of Mavacuran Alkaloids through Intermolecular 1,4‐Addition of an Organolithium Reagent**" @default.
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- W4327733599 doi "https://doi.org/10.1002/ange.202302461" @default.
- W4327733599 hasPublicationYear "2023" @default.
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